Sodium Carbonate → 4-(3',4'-Dichloro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester

HRID 381857

Reaction equation

HRID 381857 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][C:7]=1[Cl:8].Br[C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[CH:14]=[CH:15][C:16]([C:19](=[O:26])[CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:17][CH:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 838865Methyl 4-(4-bromophenyl)-4-oxobutanoateHCID 27343303,4-Dichlorobenzeneboronic acid

Product 1

HCID 865835194-(3',4'-Dichloro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

In a manner similar to Example 12, Step (b), (3,4-dichloro-phenyl)boronic acid (1.0569 g, 0.005539 mol) was allowed to react with 4-(4-bromo-phenyl)-4-oxo-butyric acid, methyl ester (1.3636 g, 0.005019 mol) in the presence of tetrakis(triphenylphosphine(palladium(0) (0.1054 g, 0.0000912 mol) and 2.0 M aqueous sodium carbonate (5.5 mL, 0.011 mol) in toluene (11 mL) to give, after chromatography on silica gel (270 g, 230-400 mesh), eluting with hexanes-acetone (7:1) 1.432 g of 4-(3′,4′-dichloro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a white solid: mp 120-121° C.

Workup

  1. customto give
  2. washafter chromatography on silica gel (270 g, 230-400 mesh), eluting with hexanes-acetone (7:1) 1.432 g of 4-(3′,4′-dichloro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a white solid

Sources & evidence

ORD record
ord-1af08d6387ee4d3b9a858f098df12c36
Source dataset
uspto-grants-2001_10
Patent number
US06307089B2

Linked notes

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